| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 3:45 PM | Varsity | League | Normal | Away | Conard | | | | Reservoir Rt. 4 - Reservoir Rt. 4 | 2:15 PM |
| Southington | | |
| WED 9/18 | 3:30 PM | Varsity | Non-League | Normal | Away | Lewis Mills | | | | Lewis Mills High School - Cross Country Course | 2:45 PM - boys and girls are riding together |
| SAT 9/21 | 1:00 PM | Varsity | League | Normal | Away | | | | | Winding Trails - Cross Country Course | |
| WED 9/25 | 3:45 PM | Varsity | League | Normal | Home | Glastonbury | | | | Winding Trails - Cross Country Course | |
| Hall | | |
| SAT 9/28 | 3:15 PM | Varsity | League | Normal | Away | | | | | Wickham Park - Wickham Park | 9:00 AM - boys and girls team riding together |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Away | Simsbury | | | | Stratton Brook State Park - Stratton Brook State Park | 2:15 PM - boy and girls are riding together |
| Northwest Catholic | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Home | Avon | | | | Winding Trails - Cross Country Course | |
| TUE 10/15 | 3:00 AM | Varsity | Postseason | Normal | Away | Berlin | | | | Wickham Park - Wickham Park | 12:30 PM - Boys and girls are riding together |
| Bloomfield | | |
| Bristol Central | | |
| Bristol Eastern | | |
| Conard | | |
| East Catholic | | |
| East Hartford | | |
| Enfield | | |
| E.O. Smith | | |
| Glastonbury | | |
| Lewis Mills | | |
| Maloney | | |
| Manchester | | |
| Middletown | | |
| New Britain | | |
| Newington | | |
| Northwest Catholic | | |
| Platt | | |
| Plainville | | |
| RHAM | | |
| Rocky Hill | | |
| Simsbury | | |
| Southington | | |
| South Windsor | | |
| Tolland | | |
| Wethersfield | | |
| Windsor | | |
| Avon | | |
| Hall | | |
| Central Connecticut Conference (CCC) | | |
| TUE 10/22 | 4:00 PM | Varsity | League | Normal | Away | | | | | TBA - TBA | 2:30 PM |